2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol

Base Information

• Chemical Name: 2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol
• CAS No.: 121693-61-6
• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.391
• Mol file: 121693-61-6.mol

Synonyms:2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol

Chemical Property of 2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol

There total 6 articles about 2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

(R,Z)-8-(benzyloxy)-2,6-dimethyloct-6-ene-2,3-diol (1174400-44-2) → 2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol (121693-61-6)

Guidance literature:

(R,Z)-8-(benzyloxy)-2,6-dimethyloct-6-ene-2,3-diol; With pyridine N-oxide; potassium osmate(VI) dihydrate; zinc trifluoromethanesulfonate; citric acid; In water; acetonitrile; at 60 ℃; for 16h;

With water; sodium sulfite; In acetonitrile; at 20 - 60 ℃; optical yield given as %ee; stereoselective reaction;

DOI:10.1021/jo901243y

Reference yield: 43.0%

(2R,3S)-1-Benzyloxy-3,7-dimethyl-oct-6-ene-2,3-diol (121693-60-5) → 2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol (121693-61-6)

Guidance literature:

With 1.05 eq. powdered pyridium chlorochromate; In dichloromethane; at 23 ℃; for 10h;

DOI:10.1016/0040-4039(88)85113-X

Reference yield:

(2E,6R)-1-benzyloxy-3,7-dimethyl-2-octene-6,7-diol (130790-60-2) → 2-[(2R,5R)-5-((S)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol + 2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol (121693-61-6)

Guidance literature:

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; In decane; dichloromethane; at 20 ℃; for 4h; Title compound not separated from byproducts.;

DOI:10.1021/ja000001r

upstream raw materials:

(2R,3S)-1-Benzyloxy-3,7-dimethyl-oct-6-ene-2,3-diol

(2E,6R)-1-benzyloxy-3,7-dimethyl-2-octene-6,7-diol

Geraniol

(2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol

Downstream raw materials:

venustatriol

(1S,2R,7R)-2-Benzyloxymethyl-1,6,6-trimethyl-3,5,10-trioxa-bicyclo[5.2.1]decane